In 2014, Beijing announced that it planned to implement a new election policy that would allow Hong Kongers to choose among just a few candidates, preapproved by China, for Hong Kong chief executive, the head of the territory’s government. Hong Kongers took to the streets to protest in what became known as the Umbrella Movement. Five years later, in 2019, large protests erupted after the Hong Kong government proposed a law allowing extraditions to mainland China. The Legislative Council ultimately withdrew the bill, but pro-democracy protests continued. In response, Beijing imposed the national security law on the city in 2020. The law marked the beginning of a severe erosion of the independence of Hong Kong’s judiciary and led to the closure of several news outlets. “The ‘one country, two systems’ framework is now totally broken,” Kellogg said. Hong Kong’s court system hasn’t completely turned into the mainland’s, he added, “but it’s a shadow of its former self.”

Over the years, Apple Daily endured advertising boycotts and firebomb attacks, but it persevered as one of Hong Kong’s most-read newspapers. It supported the pro-democracy protests and advocated for greater political freedoms in the city. The tabloid also had a history of criticizing Beijing, including its human-­rights record, and of exposing corruption in Hong Kong. Under the national security law, that record of independent criticism meant Apple Daily quickly became a target.

Soon after Beijing imposed the law, Hong Kong authorities arrested Lai and other top Apple Daily editors, froze millions in the newspaper’s assets, and, in 2021, forced it to shutter. Through it all, Lai has maintained his innocence. “The core values of Apple Daily are actually the core values of the people of Hong Kong,” he testified in November 2024. Separate from the ongoing national security case, Lai was convicted of unlawful assembly for attending “unauthorized” pro-democracy protests in 2019 and 2020, and he has also served about half of a nearly six-year sentence for alleged fraud. Rights groups say those charges are politically motivated as well.

Just as his business success echoed Hong Kong’s development, Lai’s plight reflects the rapid deterioration of media freedom in the territory. In 2019, before the national security law was imposed, Hong Kong ranked 73 out of 180 countries on the World Press Freedom Index; by 2025, it had dropped to 140. “Hong Kong is rapidly going in the direction of China, where there’s no press freedom,” said Aleksandra Bielakowska, an advocacy manager at the Reporters Without Borders office in Taiwan. (Bielakowska was deported from Hong Kong in 2024 when she traveled there to monitor Lai’s trial.) Lai is one of more than 1,900 political prisoners in Hong Kong, according to the Washington-based Hong Kong Democracy Council. A billionaire at one time, Lai had the means to flee Hong Kong and knew he would likely be imprisoned if he didn’t. Simon said he spent months trying to persuade Lai to escape to Taipei or London, but “the boss,” as Simon still calls him, always refused. Lai stayed because he felt a duty to defend Hong Kong. In doing so, activists say, he became a symbol of the pro-democracy movement.

The most serious charges lai faces fall under the national security law and come with a potential life sentence. Lai has been accused of two counts of “conspiracy to collude with foreign forces” to undermine Beijing’s authority over Hong Kong. Prosecutors allege that Lai asked the United States and other countries to impose sanctions or “engage in other hostile activities” against China and Hong Kong in response to the crackdown on the pro-democracy movement.

In court, prosecutors asked Lai about his links to dozens of foreign individuals, including activists, academics, journalists, former Taiwanese president Tsai Ing-wen, and Donald Trump. Prosecutors also pointed to Lai’s 2019 meetings in Washington with US officials, including then–Vice President Mike Pence, then–Secretary of State Mike Pompeo, and then–House Speaker Nancy Pelosi.

Lai doesn’t deny those high-profile connections, but he said they don’t amount to foreign collusion. He testified in 2024 that he never tried to influence foreign policy on Hong Kong or China through the officials he met overseas or asked them to take action against either party.

In the United States, the Hong Kong pro-democracy movement has enjoyed bipartisan support for years; Lai’s supporters likewise hail from both sides of the aisle. Pelosi, who met the businessman in 2019 and now calls him a hero, told me recently, “Jimmy’s case is really a case about courage. This is a martyr for democracy.” Republicans agree. “He’s so committed to his fellow Hong Kongers and to human rights in general,” Representative Chris Smith, a New Jersey Republican, told EWTN, the Catholic media network, in August.

Lai’s cause is helped, some China experts told me, by the fact that US law­makers like being tough on Beijing, and citing its poor human-­rights record is one way to do that. In September, in a letter to Marco Rubio, a bipartisan group of senators urged the secretary of state to do more to secure Lai’s release. “Mr. Lai’s imprisonment has galvanized both Democrats and Republicans in the United States and sparked concern around the world, underscoring the need to act now,” they wrote.

In addition to being accused of “conspiring” with foreign forces, Lai has also been charged under a colonial-era law for “conspiracy to publish seditious publications.” For this charge, prosecutors cited more than 150 Apple Daily articles—several of which Lai himself wrote—as examples of “seditious publications.” In one 2019 article cited by prosecutors, Lai wrote that if the extradition law passed, another “June 4th massacre” could happen in Hong Kong, referring to the 1989 Tiananmen Square massacre. “All I said in this article was the true reflection of the facts I perceived,” Lai testified in November 2024. “And the true thoughts of my heart, without any sense of hostility or intention to be seditious. And this goes for all my other articles.” As someone who supported peaceful protest, Lai told the court that he opposed violence. He also testified that he viewed advocating for Hong Kong’s independence as “a reality too crazy to think about” and banned discussion of it by his paper and staff.

Lai’s trial was expected to last about 80 days, but it has been drawn out by multiple delays. Sometimes the judges haven’t given a reason; other times, they’ve pointed to bureaucratic issues like scheduling conflicts. Gallagher believes the delays are also intended to make journalists and foreign governments forget about Lai and stymie the campaign’s momentum. “It’s more and more difficult to get engagement when there isn’t an obvious news hook,” she said. In my own experience covering Lai over the past few years, I reported on his case mainly during key moments in the trial and when the international legal team visited Washington, where I’m based, to lobby the US government. After a six-month delay, final arguments in the trial were set to begin on August 14, but the court postponed the hearing by a few days after Lai’s defense said he was experiencing heart palpitations.

In a nearly 700-word e-mailed statement, a Hong Kong government spokesman said human rights “have always been robustly guaranteed,” including media freedom. “The rule of law in Hong Kong is strong,” the spokesman said. “These principles also apply no differently in the case of Lai Chee-ying,” he added, referring to Lai by his Chinese name. Any statements that the Hong Kong government believes are intended to interfere with Lai’s case are “very likely to constitute the offence of criminal contempt of court or the offence of perverting the course of justice,” the spokesman said.

In November 2024, days before Lai began testifying in his trial, Gallagher prevailed in her argument before the UN Working Group on Arbitrary Detention, which ruled that Lai was being unlawfully and arbitrarily detained in Hong Kong. Established in 1991, the working group, a quasi-judicial body composed of human-rights experts, considers the deprivation of liberty to be arbitrary if it falls under at least one of five categories, including if the detention is retaliation for the exercise of rights protected under international law or if international norms regarding fair trials are being ignored in a way the group deems severe.

In its opinion, the group stated that Lai’s imprisonment amounted to arbitrary detention because he had been arrested and detained as punishment for exercising his rights to freedom of expression and peaceful assembly, both of which are protected under international law. The finding also said Lai’s detention violated his right to a fair trial. “The appropriate remedy would be to release Mr. Lai immediately,” the UN body said. The Chinese and Hong Kong governments did not reply to the working group’s requests for detailed information on Lai’s case and for clarification on the legal provisions being used to justify his detention.

That designation of arbitrary detention was the result of nearly two years of intense work by Gallagher and her colleagues. The Working Group on Arbitrary Detention is little-known outside international law circles, but its obscurity belies its significance. The determination was a major win for the campaign, Gallagher said, because it meant that, at least in theory, it had proved its case: that Lai’s imprisonment violated international law.

Although a positive development, the designation by itself was never going to be enough to free Lai, because there is no way to compel Hong Kong to release him. “Winning the argument on paper still results in Jimmy behind bars,” Gallagher told me. But the designation is nonetheless an important element of the campaign; the team needs it to prove to governments like the United States’ that Lai is being arbitrarily detained in order to justify their taking action on his behalf.

When it comes to arbitrary detention, some governments are transparent about what they want in exchange for a prisoner’s freedom, Gallagher told me. Russia, for instance, is upfront about asking for prisoner swaps. In 2024, Evan Gershkovich, a Wall Street Journal reporter who was imprisoned by Russia for nearly 18 months on espionage charges, was released in a prisoner exchange that included a convicted Russian state assassin held in Germany. And Iran isn’t shy about asking for money. But over the years, Gallagher has learned that Beijing is much less forthcoming about what it wants, which makes it harder for the legal team to figure out what levers they should pull to get Lai released.

“You’re operating in the dark,” said Martha Spurrier, another lawyer on the team. “It’s not about silver bullets. It’s about lots and lots of jigsaw pieces of a very big puzzle.”

Raised in Dublin, Ireland, Gallagher has worked as a barrister at Doughty Street Chambers in London for more than two decades. Earlier in her career, she worked on human-rights cases in the United Kingdom, including one in which she represented bereaved families and survivors of the July 7, 2005, suicide attacks targeting commuters on London’s public transport system. She eventually began taking on international cases, and a few years ago, she decided to focus solely on major international cases like Lai’s.

Alongside her colleague Amal Clooney, Gallagher represents Ressa, the journalist who has faced several decades in prison in an ongoing case in the Philippines over alleged cyber libel and financial crimes, which she denies. Gallagher also represents the imprisoned Guatemalan publisher José Rubén Zamora, who is being targeted with money-laundering charges, and the family of Daphne Caruana Galizia, the Maltese journalist who was assassinated with a car bomb in 2017. Gallagher is drawn to these types of cases because they underscore systemic press-freedom issues; the attacks on prominent figures are designed to undermine the entire media ecosystem in the country in question, she explained.

Figuring out how to get justice for targets of state suppression requires both luck and ingenuity. In her work on Caruana Galizia’s assassination, for example, Gallagher relied on an esoteric piece of Maltese legislation to pressure the government to launch a public inquiry. Had she followed the standard legal path, it would have taken nearly a decade to achieve a semblance of justice for the journalist’s murder.

On a rainy day in May, Gallagher and her colleague Tatyana Eatwell traveled from London to Geneva, the home of the UN Human Rights Council, to advocate for Lai. Their first stop was the British Mission, which was hosting an off-the-record briefing by Gallagher and Eatwell for nearly 20 states on the latest developments in Lai’s case. In these kinds of meetings, Gallagher said the goal is to persuade states to publicly raise Lai’s case during Human Rights Council sessions to put more pressure on China, which cares deeply about its reputation within the UN system, especially regarding human rights. “This kind of preparation work is key,” Gallagher said. In the lobby, a British Mission staffer told me I couldn’t observe the meeting, because the other states didn’t want China to know they had attended.

After the briefing, we took a taxi to a nearby café, where Gallagher and Eatwell met with a staffer from the UN Human Rights Office who works on China. Both meetings took place outside UN buildings because the various missions and the UN staffer were worried about potential repercussions if Chinese officials spotted them with Gallagher. The UN staffer sat facing the door so he could watch who entered the café. “Even the UN buildings themselves don’t feel safe when you’re talking about this case,” Gallagher said.

Gallagher and her colleagues have faced numerous threats for representing Lai. Chinese officials have called them criminals and threatened them with prosecution, so the team avoids traveling to countries that have extradition agreements with China. In Geneva, Gallagher and her team have been followed and photographed, including in their hotel and around UN buildings. “We’ve stayed in some pretty awful Geneva hotels,” Gallagher said, because the nicer ones closer to the UN are considered hotbeds of surveillance.

Gallagher and one of her children have received graphic death, rape, and dismemberment threats over e-mail and social media. There have been hundreds of attempts to hack Gallagher’s bank account, and once there were 32 simultaneous attempts to hack her e-mail account using virtual private networks that made it appear as if the perpetrators could be anywhere—say, in the United States or in Kazakhstan. She and her colleagues have also been the objects of “privilege phishing,” attempts to persuade targets to reveal sensitive information, including by creating e-mails that appeared as if they were sent by Gallagher or her colleagues. The team’s clerks and researchers have been targeted as well, including one whose iPhone was cloned. Gallagher believes the sophistication of these attacks, plus the coordination of the e-mails and cyber-attacks and the fact that they have coincided with key moments in the trial, suggest that at least some of them are likely state-linked. A Hong Kong government spokesman said that anyone who thinks they’re being intimidated or harassed should contact local law enforcement. The spokesman did not respond to questions on the other incidents, including the phishing attempts.

The harassment, Gallagher said, is another reminder of just how precarious Lai’s position is. “If this is how much they hate the international lawyers working on the case, just think about how much they hate our client,” Gallagher told me.

One of Gallagher’s most difficult battles has been with the British government, which she said missed multiple opportunities to stand up for Lai. In cases like his, government support is important, but the United Kingdom has been reluctant, Gallagher said. David Cameron was the fourth foreign secretary to hold the position after Lai’s arrest in 2020, but he was the first to acknowledge that the publisher was a British citizen and call for his release. Cameron made the statement the day before Lai’s trial began in December 2023.

Gallagher has been unable to secure a meeting with Keir Starmer, the prime minister since July 2024, to discuss Lai’s case, even though before entering politics he was a human-rights lawyer and cofounded Doughty Street Chambers, the home of the Lai campaign. Gallagher, who overlapped with Starmer at the chambers for several years and still considers him a colleague, thinks they have a fundamental difference on strategy. From Gallagher’s perspective, Starmer is trying to warm up relations with Beijing in the hopes of having difficult conversations in private. “That’s the wrong strategic approach,” she told me. “When dealing with the CCP [Chinese Communist Party], it is a mistake to give away the prizes and to give away the leverage that you have before you’ve got anything in return.” The UK’s “softly, softly” approach, as Spurrier calls it, means the government is squandering what leverage it does have, such as its ability to approve the controversial “super-­embassy” that China wants to build in London or its ability to lift sanctions on Chinese officials.

The legal team regularly lobbies members of Parliament to put pressure on ministers by writing letters, passing motions, and asking questions about Lai during debates or prime minister’s questions. “The only way you can force them to operate in the way you want them to operate is if they feel the political pressure,” Spurrier said. Some members of Parliament, like Calum Miller, share Gallagher’s view that the United Kingdom shouldn’t discuss trade with China—or trust China as a trading partner—until London and Beijing seriously engage on Lai’s case. With other MPs, Gallagher has a different edge because of a recent influx of about 150,000 Hong Kongers, who were given visas after the national security law was imposed and who can vote in British elections. It’s in the political interest of the lawmakers who represent them to be strong on Hong Kong and defend Lai.

Meetings with lawmakers are also intended to generate public pressure through media coverage. After Gallagher met with Conservative MP Suella Braverman in May, The Telegraph published an article about Braverman’s criticism of the Labour Party’s response to Lai’s case. “If the Prime Minister still held the convictions of a human rights lawyer, I have no doubt he would be acting on behalf of the Lai family. Why the silence now?” Braverman was quoted as saying.

The UK’s lackluster response isn’t limited to Lai’s case, said Fiona O’Brien, the UK director of Reporters Without Borders, who points to the British and Egyptian writer Alaa Abd el-­Fattah, who spent most of the last decade in prison before finally being released in September. The British government is siloed, O’Brien said, so elevating these cases from the foreign office to the attention of Downing Street can be difficult. David Lammy, who was recently appointed deputy prime minister after serving as foreign secretary, pledged while he was a member of the opposition to appoint a special envoy to help secure the release of British citizens detained abroad without a fair trial. That plan appears to have been placed on the back burner over concerns that it could harm the UK’s trade relationships, The Guardian reported. “It is their duty and their responsibility to champion his cause,” David Alton, a member of the UK’s House of Lords, said of Lai. “In reality, trade deals seem to matter more.”

In an e-mailed statement, a Downing Street spokesman did not respond to questions about criticism that the British government appeared to prioritize trade with China over Lai’s release and that Starmer has not met with Lai’s legal team. “British national Jimmy Lai’s case is a priority for the UK Government,” the spokesman said. “We continue to call on the Hong Kong authorities to end their politically motivated prosecution and immediately release Jimmy Lai.”

Lai’s son Sebastien joins most of Gallagher’s meetings with members of Parliament. Sebastien became the campaign’s public face shortly after Gallagher was hired to lead it. The importance of family members in these kinds of campaigns is another lesson Gallagher has learned from previous cases she has worked on or observed. For example, when the British Iranian dual citizen Nazanin Zaghari-Ratcliffe was detained in Iran from 2016 to 2022, significant public pressure from her husband, who was represented by Eatwell, proved to be pivotal in pushing the British government to pay a £400 million debt to Iran to secure Zaghari-Ratcliffe’s release.

Maintaining pressure—and public interest—can be difficult if the campaign doesn’t involve someone with a blood connection to the prisoner, Gallagher said. When Sebastien talks to lawmakers and officials, he tends to speak not of Lai the businessman but of Lai the father. After an event organized by the team in London in May, in which it released a letter signed by 22 former political prisoners and their families urging Starmer to do more for Lai, Sebastien told me he aimed to convey that in addition to being a pro-democracy figure, his father is also a human being and a beloved member of the family. “He’s also someone that wants to be back here and just spend the remainder of his days with his family,” the younger Lai said.

In some ways, the legal team wants the guilty verdict to come sooner rather than later. If the team thought there was even a slim chance that Lai would be acquitted, they would pour all their efforts into that hope. But Gallagher said that Lai will almost certainly be convicted and sentenced to prison for the rest of his life. Once he is found guilty, which is expected before the end of the year, it will open up additional levers that the team can use.

Throughout Lai’s case, Hong Kong authorities have deflected criticism of Lai’s detention by telling foreign governments and the media to let the judicial process play out. Prolonging the trial “just staves off international criticism,” Gallagher said. “The excuses will be gone when he’s convicted.” Another factor, she continued, is that some governments don’t comment, as a matter of policy, on ongoing legal proceedings in other countries, but they might be more outspoken once Lai is found guilty. The legal team hopes that Beijing will be satisfied with the trophy of a guilty verdict and then be open to a deal, such as releasing Lai for time served or offering compassionate release because of his age and health issues.

Still, a conviction may exacerbate a problem that the campaign has faced all along. Once Lai is convicted and sentenced, there won’t be any more court hearings to generate media coverage or political interest. That’s why Gallagher believes these final weeks before the probable conviction are key: “This is the time at which maximum pressure must be applied.” The longer the legal case goes on, Gallagher said, the greater the chance that Lai will die in prison. But Gallagher doesn’t think China wants that to happen, because then he’ll become even more powerful as a martyr, like Liu Xiaobo, the Chinese human-rights activist who died from liver cancer in state custody in 2017.

“What’s at stake here is a man’s life, and as matters currently stand, he’s going to die behind bars,” Gallagher said. “We’re doing all we can to stop that.”